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Cyanocobalamin

Catalog No. DB00115 Name DrugBank
CAS Number 68-19-9 Website http://www.ualberta.ca/
M. F. C63H88CoN14O14P Telephone (780) 492-3111
M. W. 1355.365181 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 2

SYNONYMS

IUPAC name
cyano[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16Z,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-(2-{[(2R)-2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl]carbamoyl}ethyl)-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1?,?.1?,??.1??,??]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
IUPAC Traditional name
cyano[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16Z,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-(2-{[(2R)-2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl]carbamoyl}ethyl)-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1?,?.1?,??.1??,??]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
Brand Name
Cyomin
Dicopac
Nascobal
Rubramin PC
Anacobin
Bedoz
Berocca PN
Berubigen
Betalin 12
Cernevit-12
Cobavite
Cobex
Cobolin-M
Crystamine
Crysti-12
Cyanocobalamin Co 57 Schilling Test Kit
Cyanoject
Depinar
Dicopac Kit
M.V.I. Pediatric
Neuroforte-R
Primabalt
Redisol
Rubivite
Vitabee 12
Rubratope-60 Kit
Vibal
Shovite
Vi-Twel
Rubratope-57 Kit
Vibisone
Vitaped
Ruvite
Synonyms
Vitamin B12
Vitamine B12
Cyanocob(III)alamin
Vitamin B12 complex

DATABASE IDS

CAS Number 68-19-9
PubChem CID 44176380
PubChem SID 46509031

PROPERTIES

Solubility 12.5 mg/mL [MERCK INDEX (1996)]

DETAILS

Description (English)
Item Information
Drug Groups approved; nutraceutical
Description Cyanocobalamin (commonly known as Vitamin B12) is the most chemically complex of all the vitamins. Cyanocobalamin's structure is based on a corrin ring, which, although similar to the porphyrin ring found in heme, chlorophyll, and cytochrome, has two of the pyrrole rings directly bonded. The central metal ion is Co (cobalt). Cyanocobalamin cannot be made by plants or by animals, as the only type of organisms that have the enzymes required for the synthesis of cyanocobalamin are bacteria and archaea. Higher plants do not concentrate cyanocobalamin from the soil and so are a poor source of the substance as compared with animal tissues. Cyanocobalamin is naturally found in foods including meat (especially liver and shellfish), eggs, and milk products. [HMDB]
Indication For treatment of pernicious anemia (due to lack of or inhibition of intrinsic factor) and for prevention and treatment of vitamin B 12 deficiency.
Pharmacology Cyanocobalamin (Vitamin B12) is a water-soluble organometallic compound with a trivalent cobalt ion bound inside a corrin ring. It is needed for nerve cells and red blood cells, and to make DNA. Vitamin B12 deficiency is the cause of several forms of anemia.
Toxicity Anaphylactic reaction (skin rash, itching, wheezing)-after parenteral administration. ORL-MUS LD50 > 8000 mg/kg
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Readily absorbed in the lower half of the ileum.
Half Life Approximately 6 days (400 days in the liver).
Protein Binding Very high (to specific plasma proteins called transcobalamins); binding of hydroxocobalamin is slightly higher than cyanocobalamin.
References
Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. [Pubmed]
Sharabi A, Cohen E, Sulkes J, Garty M: Replacement therapy for vitamin B12 deficiency: comparison between the sublingual and oral route. Br J Clin Pharmacol. 2003 Dec;56(6):635-8. [Pubmed]
Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. [Pubmed]
Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. [Pubmed]
Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. [Pubmed]
External Links
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REFERENCES

  • Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. Pubmed
  • Sharabi A, Cohen E, Sulkes J, Garty M: Replacement therapy for vitamin B12 deficiency: comparison between the sublingual and oral route. Br J Clin Pharmacol. 2003 Dec;56(6):635-8. Pubmed
  • Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. Pubmed
  • Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. Pubmed
  • Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. Pubmed